1. Let yourself try things that are widely seen as lazy and indulgent.
Melissa was great at everything when she was a kid. She was a math major in college while she was teaching herself to be fluent in Mandarin. She got a job in investment banking.

Which reminds me of when I graduated from college and all I did for five years was play volleyball and read. I read a book every night. I was so excited to be able to read whatever I wanted instead of being crushed by assigned reading. There is this window in life, between graduating from college and having kids, when life is a library.

If that thought resonates with you, you will love this book: The Night Bookmobile. Melissa sent it to me. As a gift. She didn’t add a card, so I assumed the publisher sent it to me for review. And I loved it so much that I sent a copy as a gift to Melissa.

Melissa has Asperger’s, which, in her case comes with a photographic memory. There are some things a photographic memory cannot help with: how to tell Steven’s mom she is not going to baptize her kids. But there is a lot a photographic memory is good for, like making tons of money in banking, which Melissa ruled out because of long hours.

3. Get other opinions. All top-performers have lots of coaching.
Naturally, Melissa gets free career coaching from me.

That’s a picture of her bank lobby. One of the reasons Melissa’s job is good for her is that she can bring her dog to work.

4. Recognize the difference between a career and a hobby.
I told Melissa that she should leverage her photographic memory to do a job she would actually like. She is experimenting. She launched an Etsy store.

She specializes is mid-century modern. I would not say Melissa has a great eye for design, but she is great at memorizing what everything is worth, and she knows what’s under-priced. The problem is that she is very excited about decorating her new house and it seems to me that the Etsy store has morphed into a holding ground for the stuff she is about to put into her house.

Here’s the result:

The problem with the Etsy store idea is that it doesn’t scale. She’s never going to make enough money to pay for the (eventual) childcare she’d need in order to run around Austin sourcing mid-century modern stuff from design-deficient sellers on Craigslist.

“You can’t keep building the Etsy store,” I told her. “It’s not a business. It’s a hobby.”

5. Take suspiciously awful opportunities. They might lead somewhere good.
Luckily, Melissa grew up as a rich kid (whose mythical trust fund is tied up until she can figure out how to create a life her dad likes, which, frankly, will be never when we are starting with a junk shop online and New Yorkers in bed). In case you don’t know the benefits conferred on rich kids, here’s a snapshot:

Melissa picks up her phone and it’s her mom’s friend. Her mom is a doctor. Her mom’s friend is a lawyer. And her mom’s friend has a client in the Middle East who has a textiles business, and a meeting set up with Nordstrom to sell stuff to them. The lawyer wants Melissa to represent the textile firm to Nordstrom.

Not that Melissa knows anything about textiles. Or the Middle East. But so what?

She decides they need a lookbook – which is how you pitch high-flying buyers on products that have to look expensive and precious. Melissa is a great photographer who never markets herself, so it’s the perfect storm.

She takes photos of the stuff. With her friend who is not a model but looks like a model because all girls who go to expensive private schools look like models.

Then, at Nordstrom, Melissa meets all sorts of budding entrepreneurs who need lookbooks. Melissa makes the sale to Nordstrom, because Melissa can sell anything if she tries. Then she collects all the business cards of people who want Melissa to photograph their product.

Just like that, Melissa has a new, exciting job.

6. Forget conventional ideas of a good job. A good job feels good to you.
Then she goes back to her hotel and sleeps. For a day. Then she goes home. And she is so happy to go back to her job, which, previously I have said is sort of a stupid job, but it’s a job that is routine and predictable, and the people are really nice, and Melissa likes it.

Melissa wants to just get married and have kids. But she knows she would be bored staying home all day with kids. She is trying to figure out where the engaging, not-so-intense jobs are. They are hard to find. Intensity and engagement usually go together.

To be honest, I helped Melissa start her own business three times. We got funding for her company, but then she didn’t like the high-risk nature of a start-up, so we didn’t do it. She said she wanted to turn her photography into a business. So I showed her how to do that, and we got it all set up, but she realized she hates marketing herself. Then we made a plan for her to turn textile sales into a consulting business.

But she doesn’t want a business. She wants to work for someone else. Which is, actually, much more common than you think. It’s just so unfashionable to admit that.

You never know, really, if you want a business until you have a business sitting right there that you can run. I think that’s the best thing I can teach you in the webinar: how to learn about yourself and how to figure out what sort of work you need day-to-day to feel fulfilled. For so many people, trying to launch their own company is a really important part of this self-exploration.

Back to Melissa. She’s the guest moderator on Thursday night. She will be great. Because she’s great at everything she does. I will ask her to do it again on the Friday session, and she’ll say no. We don’t know why she’ll say no until she does Thursday. That’s the best way to know what you don’t want to do, right? To try it.

I absolutely adore that quote as well. :) I’ve been averaging a book per week since graduating 1.5 years ago, so can completely relate to that quote. However, now I’m terrified to have kids and lose this wonderful free reading time.

This is a great. I think it is encouraging to read about individuals who view their career as trial and error. For me, trying to develop a brand and creating a freelancer lifestyle is so different and new. I like the challenges which is why I blog about it. Best of luck to your friend and her business venture.

I’m in a similar spot to Melissa. I was in construction (I’m a woman) and it paid amazingly and the main requirement is that the job be your entire life.

So when I got laid off, I spent a 18 months trying to figure something else out (including my own bakery), and keep going from marginally related job to marginally related job. Part of the problem is I get hired by people who think they need a person with construction expertise. And they do, but they only need that for like 20 minutes a week.

I’m working at a church now, bored out of my mind, but I get to go home at 5 and half day every Friday with paid benefits. So, in a stable low-engagement, low risk job.

Trying to figure out what I can do when I hopefully start baby making next year.

This sounds like my situation. My job is also stable, low-risk, and low-engagement, and I am also bored out of my mind. The pay and benefits are great, and I don’t *hate* it per se, but it’s such a dumb job.

As the economy continues to worsen, I lower my expectations more and more, and I read about other people’s problems and consider myself lucky just to have a job at all and not have to worry about money.

But still, there are those times I think about the kind of job I *do* want – a controller position for a small company – and wonder if it will ever happen. I am always looking, but they are very few and far between, and they always seem to want some odd, specialized piece of experience or industry background that I don’t have.

First, great post, Penelope!
I was in a similar situation. Leaving my secure job was one of the most stressful occasions in my working life. I have spent years as part of an organization but at some point I found my career at a dead end in my current workplace and I realized my full potential in another position. It was time to change my career. But in my opinion sometimes it isn’t easy to transmit theory into practice. I got help from a personal online coach where I received really good advice. We have analyzed my skills, created an action plan to get clear achievable next steps and in addition I have received help to get rid of my blocks, fears and insecurities. I felt so much more energized, comfortable and confident (I really can recommend Your24hCoach) to transmit the tips into real action and proof in daily life. Good luck, everyone!

I am half-contented with working for my dad just because I sit around all day and read New Yorkers. I always wanted to be a spy, which turned into the slightly-more realistic desire to work for the state department. And I just got my American citizenship last week (thank god) so I could actually start working towards something like that. Except I am just getting comfortable reading New Yorkers, and running twice a day with my dog, and living in Charlotte. And really I should be learning Arabic or something. So maybe I don’t want to do that. And I’m thinking a little more seriously about my startup idea, but I’m not sure if I’d really want to do that either.

I just started going to a personal trainer this week. My friend won a month of free sessions but the gym was too far away so she gave it to me. And I love it, because I love working out but I am lazy. So really, I love working out if someone is yelling at me and giving me something to prove. And so maybe I’m like that at work, too.

Congratulations on citizenship! And that you could followup a citizenship announcement with that you think you should be learning Arabic –that’s like a political poem that only you could write, Harriet!

Be careful with the State Department jobs. Many of their jobs – especially in DC – are government grind jobs. My sister worked for awhile at the State Department Credit Union at their main office in DC. She has worked her entire career in sales & marketing and she considered them the worst customers of her career. They were always rude, and unhappy. She could only imagine what type of work environment did this to everyone.

The State Dept. has >60,000 employees. There are lots and lots of opportunities, so don’t let tales of angry credit union customers deter you. I knew some folks who liked to travel, and others that preferred the day-to-day grind in DC. You can make your own path. Good luck!

Posted by I used to contract w/ State
on October 26, 2012 at 4:50 pm
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“A good job feels good to you”.

So true. It helps if the job pays well enough to live comfortably too.

I’m charmed by all these thoughts that I can simply be me, strengths and weaknesses, likes and dislikes, and back my way into a life that is tailor made for me. Maybe it’s my Gen X upbringing, though, that keeps insisting in the back of my mind that no matter what life I back into, there will be SOME part of it that I don’t like and that rests in my weaknesses. I’ve found that my greatest life triumphs, both personal and at work, have come when I’ve pushed through those things and done well anyway. That doesn’t mean I have to look for those situations — why deliberately seek suffering? But I’ve not gotten any better or had any more fun by shirking them either.

I just spent a week with my family, including an aunt. I sat down to tell her how much I was enjoying my job, and she goes:

“You should be looking for a new job. They don’t pay you enough. I wish you had gone to business school. You’re wasting your potential.”

And I’m sitting there, just flabbergasted, so I drop the subject.

This is a woman who, after calling for my mayonnaise recipe, launched into a vicious, unprovoked tirade about my cousins:

“I’m disgusted by my nieces. They’ve given up their careers so that they can be broodmares to their idiot husbands. My generation fought so hard so that they can have impressive careers and they’ve just said ‘Nope, not interested.’ They had so much potential and they’re wasting it.”

And I have realized that I have spent a lifetime and a small fortune on therapy trying to tune out people (and inner voices) like my aunt. All I want for myself is the confidence to own my choices and not apologize for them to anyone, least of all my bitter and angry aunt.

Margaret M, your comment resonated with me because tuning out family members has been huge with me finding self-acceptance and happiness with myself and my choices in life and work.

So much of our satisfaction with life/work is tied to things we can’t control, like the misguided opinions of unhappy people around us or unfortunate life circumstances that we can’t change, but have to bear until the situation plays itself out over time, like a sick spouse or parent passing on. Those things are just depressing and we can’t change that, so we’re unhappy for a time.

It took me 35 years to learn who to tune out and for outside circumstances to change to a point where I could actually be happy without feeling guilty about it.

When we’re not in control is when we’re the most unhappy. That’s why sitting around and reading all day feels good. No one is telling us what to do or trying to make us feel bad.

I realized that listening to the opinions of bitter relatives or, in my case, a judgmental father, gives them control. I’ve learned not to give over that control anymore and just do whatever the hell I want. I don’t give their opinions any weight, and now I just live. I’m happy.

When I quit my full-time gig to open my guitar studio, several family members flipped their lid. Immediate family members. I said f@#k ’em and never looked back. People have enough difficulties to overcome when trying to figure out their careers. Family, the only ones who seem to be the least but interested, cannot be allowed to be poking their big snouts around in career decisions, or any other ones for that matter. The fewer hours I work and the more I make, the more they wig out too. Put the kibosh on the peanut gallery by reveling in it and living well.

I love your blog, but found this post to be disappointing. Granted, I have a career that I am happy with (after several failed iterations through careers that I was NOT happy with). So perhaps I’m not your target audience for this post. This post seemed like great advice for people like Melissa, who have the luxury of money, which gives them more freedom. For people who are living on a tighter budget, I think career searching is more challenging. I guess I was expecting more suggestions geared to readers like that.

Melissa actually lives on very little money. And until she opened up her Etsy store, all her possessions fit into about ten boxes.

It’s true that Melissa doesn’t have student loans, but it’s also true that anyone can live like Melissa. To be clear, she does not have family money. They don’t give her any. So she is like a former-rich kid with very little savings. What she does is:

1. Doesn’t do very much besides her daily routine, so she doesn’t spend a lot of money.

2. Doesn’t own a lot of stuff and doesn’t worry about saving for a house, kids, etc. because she accepts that she won’t be able to accumulate a bunch of money.

If you have student loans, that would make you different from her, but honestly, if you pay the minimum on your student loans for your whole life, it doesn’t change your cost of living very much. It’s a mental game — you tell yourself having the loans doesn’t matter, it’s like a monthly tax.

So, that way, you can take a low paying job all the time.

Melissa likes having very little pressure at work. She wishes she could handle more pressure, but I don’t think she can. That route is open to anyone. But first you have to decide you want a low-stress life more than you want a life of achievement. That, to me, is the most difficult part of Melissa’s life for any of us to mimic.

She may live on very little now, but just being a former rich kid resulted in the opportunity to consult for an international textile firm and sell a lookbook to a company like Nordstrom. Being rich or upper middle class means you’re much more likely to rely on opportunities or connections like that. As well as the ego to think that you deserve them/are capable. (I have no idea if Melissa has this mindset, but I’ve noticed that people from those kids of backgrounds tend to.)

This post is about my life. After a Wall Street career which I was great at but didn’t much enjoy, I decided to learn digital media hands on so I did some consulting, then ran an online parenting “blogazine”, did an interview series with female tech entrepreneurs while figuring out what I really wanted and needed to do. Good ideas take time to “marinate” and in my case, it took over 7 years for all the needed pieces to fall into place – from technology, capital, to self-confidence. I am soon launching the first ever shopping site at the intersection of limited edition designer goods and philanthropy, and although it took some time to “get” here, I feel like every moment was necessary to be where I am right now.

0. Surprise!
I think PT is just as human as the rest of us when it comes down to frank, unfiltered criticism of a good friend. :)

I do not hear her singing the praises of Melissa’s current job for the rest of those who are at the age/stage of Melissa. Esp. if Melissa has such a wide pallet of options and a guy in the wings to marry…

shouldn’t she be hitting the boards every day aggressively trying and testing so she can get her ducks in a row with interesting part time work in place before babies? Penelope, where’s that whip you use on the rest of us?

…case in point, that of the yoga teacher…google that interview and you’ll never be able to look your yogiini (sp?) in the eye again.

1. I’m buying the book
2. I was reading Little Dorrit while in labor with first child
3. I am skeptical/intrigued/curious about Melissa as moderator…will be very interested to experience that

Looking forward to the seminar…$$$$$$ anybody out there who’s on the fence, just make the investment.
I’ve had career counselling with Penelope, and even though I’ve had a great career, she impresses me as a gifted, valid, seer who can give to others the tools to capture the Black Swans. $$$$$$

Lynn, you make me laugh. You have done such good research to find the interview with the yoga teacher. I don’t think I ever knew that one was online.

Yoga teacher background: the woman wanted to run a yoga business so she could teach yoga, but running a yoga business is all about marketing. It’s very difficult to differentiate yoga teaching enough to capture market share. And the yoga teacher wants to do yoga, but not marketing. So that business idea won’t work.

It all has to do with what someone’s goals are. Lynn, you are a total go-getter. You need to change the world. So if you told me you want the job Melissa has I’d tell you you’re out of your mind.

But Melissa has absolutely no need to change the world. There are a lot of people like that. People who want to change the world can’t imagine that not everyone wants to do it. But it’s true: not everyone has that as a goal.

So Melissa’s goal is to have a clam, low-stress, predictable life. I force Melissa to see the reality of her life in the same way I force the yoga teacher to see it. Melissa was stuck, for a long time, feeling that she needed to have impressive achievements in her adult life in the same way she did during the childhood. But she doesn’t. Just because people expect her to be a high earner at work doesn’t mean she needs to do that.

I completely agree that one has to realize whether a more high pressure or low pressure job is the way to go. I am just wondering a little what drove Melissa as a child – and why this drive to achieve was lost. Or maybe some part of the grit to keep going despite obstacle (which is not the same thing as a high pressure job) was never taught to her? Or she never needed it and so could not develop the I-will-do-this-despite-all-the-obstacles- kind of drive (you might call it stubborness)?

And that’s not a bad way to live – a relaxed, quiet, low-key life. Some people might prefer a more exciting or engaged life, but others might just want to sit back with a cup of coffee and watch the world go by. Nothing wrong with that – everyone has their own definition of happiness.

My experience/pursuit with one sentence here – “People who want to change the world can’t imagine that not everyone wants to do it.” – led to the world changing me.
I can most identify with Richard Branson when he says his approach is “making a difference” rather than the commonly used phrase “changing the world”. Changing the world feels like to me coercing an opinion or ideology where making a difference is an outcome that’s not predetermined and enacted by the originator but rather a collaboration of all the parties involved. That’s how I interpret the difference in meaning between the two phrases. I saw him speak at a local college and occasionally read about him in the news. It’s his messages and experiences that impress me more than his money ever will. He states in a recent NPR interview – “”You have to go back to thinking: What is a business? A business is people coming up with an idea to make a difference in other people’s lives. And throughout my life, I keep on coming across situations where I feel we can do it better than it’s being done.” This rings true to me.

Great article! I’m the better for reading it. I was diagnosed Asperger a year and half ago, but it sounds like a lot of people relate to the psychological posture described here – it’s nice not to be alone!

There is another window in life where distractions are few. That one called the empty nest. It’s met with greater wisdom, greater sense of self, and even more ambition. Because the deadline is looming. There is no longer a lifetime to succeed. It’s half over. Time to get going.

Great point! My son started high school this year and I see a glimpse of the nest as I had him when I was older. I feel exactly as you state, time to get going. Do something different. If you haven’t achieved your potential, then get off your backside.

Really great article! It’s true, building a career that works for you is often a form of trial and error. Few people know exactly what they want to do with their career or, more importantly, what kind of career will work best for their lifestyle. It’s important to give yourself room to find out what kind of job is best for you. This way when you’re interviewing for your dream job, either in person or through online video, you can be positive it’s the perfect opportunity for you.

I have always known that I want to work for someone else (I’m relieved it’s unfashionable- less competition), and that I want an engaging, not-so-intense job. But they are hard to find! Especially in tech. I know so many super-brain engineers that are happy to work crazy hours for way less than they’re worth, if the job is really cool. I just have regular above average brains and can’t handle start-up hours, so I’m pretty concerned about finding a cool job (at least I don’t mind being unfairly compensated to a certain extent).

Well said!
I’m in a similar situation – also in tech – but I have the job. I’m using my brains but am not expected to put in crazy hours. In fact, my boss tracks everyone’s vacation time and encourages us to use it. He also encourages us to work from home and, when we are at the office, has been seen going around encouraging people to go home if they are staying after regular hours.
Best.boss. ever.
I don’t want to start my own company – I never have. but I want to be part of something that is growing and successful. I also want to have time for my life outside of work where I design and make costumes for theater, work in my garden, spend time with my husband and friends, and yes, read (I average about 2 books a week).
Whoever mentioned the empty nest is absolutely right. There is much more time for the good stuff. But I still need a steady job to afford college for the one child who has not yet graduated.
I guess I’m incredibly lucky to have this situation – but it has taken me a while to admit that this is what I want – because I too was conditioned to believe that I should want “more”. Perhaps it’s the wisdom and courage that comes with getting older, but I don’t feel like I have anything to prove any more. I know myself and can articulate what I want. Now I just have to get rid of the regret that I didn’t get my head to this place sooner :)

Tell Melissa not to worry about potential children and what her future mother-in-law thinks. So much can happen between now and then. It’s clear Melissa knows her own mind. Deal with it when it’s an issue, and don’t waste time on it now.

I always love articles about Melissa and this was no exception, she sounds like a very cool, complex and fascinating person who continues to change daily. I try to be open to new opportunities and try to keep an online presence which I know is important to inviting new opportunities, but it seems like for Melissa new opportunities and chances to try new things (such as moderating) fall into her lap. I know that could be the way this post is written, but is it that she’s just that connected and works her connections or is she just that lucky? Thanks so much for the post!

This article + comments have so many things wrong with it I don’t know where to start.

If you want to write an article about finding the right career by trying out the wrong ones first, fine. But your example is about a privileged woman who is changes interests month by month, and is uncommitted to do the work necessary to make it at anything. So you should have called this article “ex-rich kid about to marry rich and embark on several interesting part time careers until her trust fund kicks in.” Or change the example you are using.

Your career doesn’t have to be something world-changing. But isn’t it a waste of talent, abilities, and time to just simply do nothing?

She doesn’t have to worry about money because her family will, eventually, give her the trust fund whether it’s now or in 20 years. How many people you think have that luxury?

Meanwhile she is waiting to get married and have kids so the husband can take over paying the bills, and she can hire a nanny until she goes through a series of part time jobs. It’s fine if you want to do the stay at home thing, but Melissa can’t even commit to that completely.

If she is talented like you say she is, isn’t it terrible to say “hey, you were gifted as a child, and it’s totally ok that you’re unmotivated to do anything requiring any type of effort, because not everyone needs to change the world.”

Your comment about anyone being able to do what she’s doing is complete bs. It can happen, but not on one’s own. You said in one comment that she “doesn’t own a lot of stuff and doesn’t worry about saving for a house, kids, etc.” (And just above that, in the article you said that all she wants to do is to get married and have kids. Someone is going to be paying for that, and the mid century pieces, which as she knows with her photographic memory, are pretty expensive. )

And please abstain from giving financial advice. You said it yourself that you’re terrible with money. So to recommend that people treat their student loans like a tax bill is idiotic. Just send people over to Ramit who actually knows what he’s talking about.

Hi! I am great friends with Melissa. She is one of the most unique people I know. I could go on all day about how wonderful she is but I will keep it brief. Two things that I admire about Melissa are she is honest with herself about what she wants and needs out of life, love, pharmaceuticals, dogs, etc. and two, she is honest with others about it too. I can’t help but notice and marvel [with envy] that her ambition to fulfill an honest and real desire within herself has opened doors for her to a wide variety of opportunity. Her definition of success is intrinsic and its very refreshing to take note that when we (she) starts living for ourselves (herself) the world opens more doors than continuing to chase after someone else’s (anyone elses even S’s)vision for what our life should be. This is true in many facets of life. I take away from her to sit with myself (and an old New Yorker) and find a way to be honest and real attach my ambition to what it is that I want, quitting and starting all over the place until I find it. I love you M! I predict more doors to be flying open for you in the very near future.

This is such a good post. I’m so curious to hear what you think the difference is between Melissa’s choices and recovering from burnout? I left a high-profile job a few years ago, working for a head of state because I was “burnt out” and my life for awhile really resembled Melissa’s days: a job I could do in my sleep, flexibility to show up for my loved ones when they needed me, lots of reading and learning to cook for the first time ever in life.

I never fully shifted back to that level of high-intensity work and I don’t know if I ever will. And even though my life feels so much richer now, I’m still trying to understand why that uncertainty makes me a little sad.

I feel that I have some things in common with Melissa: a stubborn unwillingness to self-promote and an intense desire to put my family life first but stay true to myself and my own interests at the same time. Makes for an unpredictable (mostly unimpressive) meandering sort of life path. Makes me like Melissa even more, and you already know how I feel about you :)

I don’t believe these “low-stress” or “I could do it in my sleep” jobs really exist. Any job can and will get stressful if you know you have to do it to make sure you and a family have health insurance and food and shelter.

“Low stress” really means I know I have a way out and won’t have to do this forever, i.e. become a stay at home mom or marry a rich guy.

“I could do it in my sleep” really means I’ve only been doing this a short time and the long term implications of dealing with crabby co-workers and impossible to please customers has not sunk in yet.

The Drama of the Gifted Child is NOT about intellectually gifted people but rather about the adult survivors of child abuse. There are lots of good books about intellectual giftedness but this is not one of them. (It IS a good book about surviving abuse, though.)

This is a great. I think it is encouraging to read about individuals who view their career as trial and error. For me, trying to develop a brand and creating a freelancer lifestyle is so different and new. I like the challenges which is why I blog about it. Best of luck to your friend and her business venture.

Thank you for sharing this post, I 100% agree with everything. I think the “Forget conventional ideas of a good job. A good job feels good to you” tip is one of the most important. Some of us have never even questioned their idea of a good job, but there is no one single definition, everyone should have its own!

What an inspiring blog. It definitely resonates with me. Since graduating from business school, I came back to live with my mom. I had such a hard time finding a job in NJ, but once I finally did, I found that it didn’t pay what I wanted. I have since been trying to understand that even though it doesn’t pay what I want it to, it is okay for the time being because I like what I do, and I love the people I am surrounded with each day. Thanks for sharing!

Agreed. It wasn’t this post. It’s that the fiance has failed to establish boundaries with his mother. Are there really people who think religious decisions should be up to anyone other than the two parents? If he doesn’t have the spine to tell his mother when to butt out, he is too immature to get married. And how arrogant is this guy, to think that their break-up has “ruined” her life? If you ask me, she dodged a bullet.

Thank you for sharing this post, I think it is encouraging to read about individuals who view their career as trial and error. I 100% agree with everything. I think the “Forget conventional ideas of a good job. A good job feels good to you” tip is one of the most important.

Thank you for writing this post. I’m 22 and a year out of college, and have been seriously struggling. This article has just made me feel so much better about the meandering path I’m on, you wouldn’t believe. Thank you.